Craigs List Roommate free porn video

(This is a work of fiction. The people in this story are NOT real and do not represent anyone living or dead. This story also contains adult material between two consenting adults. If you are not at least 18 years of age, do not read any further. This is the first part of a presumably 2 to 3 part adventure. I suppose that would depend on the encouragement or lack thereof I receive. I do love constructive criticism and I'd like very much to hear what you think. I can be reached at [email protected] or you can leave your comments here. Please do not re-post this story without direct approval from me. ~Kaila Kane) The day had finally arrived. Nate had just turned 18 and that meant, for him anyway, it was time to leave his parents' house and get a place of his own. He was very excited to say the least. He hated living at "home". His family couldn't care less about him and it couldn't have been more evident to him. His mother was a drunk and his father was a dead beat dad that showed little to no interest in him. Although he had been saving up his paychecks from his part time job, he knew that he couldn't afford to get a place on his own. That would mean he'd have to find a roommate to share the bills with. Having no real friends so to speak, he decided to check out craigslist and see if he could find someone in a similar position looking for a roommate. After a few hours of searching the ads, he came across a post that seemed way too good to be true. It said simply, "Looking for a young male to share my enormous home with. All expenses paid. Serious inquiries contact Brad at: 714-555-8764." As I said, it seemed too good to be true. All expenses paid? Did that mean no rent? He had to find out. He decided to put his trepidation aside and call the phone number. What did he have to lose except a few minutes of his time? The phone rang a few times until a man answered. "Hello?" "Hi. My name is Nate. I'm just calling about your ad on craigslist. Can you tell me more about the offer? Are you still looking for someone?" "Hi Nate. I'm Brad. Yes I am still looking. As the ad said, I have a very big home and I'm looking for the right someone to share it with. All of the bills are paid years in advance. In fact, there would be no need for money on your part at all. Sound good?" "Well yes it does. It just seems too good to be true is all. I mean I wouldn't have to pay anything to live there?" "Nope. Not one dime. Even the meals are paid for here. Money is no problem for me. I've been very lucky in that department and I figure it's time to share what I have. No catch at all. Of course we'd have to meet to make sure you're the right candidate. Can you meet with me so we can talk about it in person?" Nate thought silently for a moment. If this were legit, this could be a dream come true for him. He really didn't have anything to lose by meeting with the guy. Sure the place was pretty far from his home but that was even better in his eyes. The further away he could get from his family, the better. He decided to take the plunge and agree to a meeting. Of course he wanted it to be in a public place so he could feel a little better about meeting a stranger. He answered. "Yes that would be fine. Is there a coffee shop or something close by that we can meet at?" "Yep there sure is. How about we meet tomorrow morning? The address is........................." "Okay sounds great. I'll see you then." When Nate hung up the phone, he was both excited and a little scared. This would be the first time he'd ever done anything like this. Meeting in a public place though was a good move. If he meet with Brad and didn't like where it was going, he could always walk away. He had to try it though. It was too good of an opportunity to pass up because of fear. That night seemed to pass by really slowly. He kept looking at the clock time and time again only seeing a few minutes pass each time. He wanted it to be morning so bad so he could just get it over with. He decided to pass the time with his favorite hobby. Now most kids his age would go to videogames as a way to keep them distracted but Nate wasn't like most kids. He was a cross-dresser. He loved everything feminine. You wouldn't know it to look at him. He was an average looking guy maybe a little on the smaller side being only 5'8" and about 110 pounds with longish, light brown hair for a guy but for all intents and purposes, he looked and acted like a normal red-blooded boy. He hid his hobby very well. He would spend hours at a time alone up in his bedroom with his door locked tight becoming Jade, his alter ego. Over the years, he was able to accumulate various articles of female clothing that he kept secure in a locked trunk under his bed. He didn't have much in there but what he had he cherished to no end. He brought out his trunk and opened it up. Inside were a few pairs of panties he had stolen from his mother's dresser along with a few bras, a couple of skirts, some tops and even a nice silk gown he got from a second hand store. He quickly got undressed and began to get dressed in his feminine treasures. He decided on going light that night because it was already getting late and he knew he'd have to be up early to get to the meeting with Brad. After getting dressed in his black silk panties and matching bra, he played with the little makeup he had scrounged up. He tried a few different techniques he had learned about from his collection of girly magazines. When he was finally done, he gazed into his bedroom mirror and fantasized about being a single girl waiting for a date. It wasn't long before he began to masturbate slowly. His orgasm was building steadily. Stroking his cock and rubbing his anus with his other middle finger was all it took for him to explode all over his stomach. After he was finished, he cleaned and washed himself up taking a long and hot shower. After drying himself off, he looked at the clock. That did the trick. It was finally time for bed. Morning came and he shot up out of his bed like a bolt of lightning. He hurried to get dressed almost tripping and falling a few times. He decided to skip breakfast. It wasn't like anything would be made for him anyway. He called a cab to the bus station and sat and waited for it to get there. The whole trip there wasn't much to speak of. It was just row of houses after row of houses then large chunks of wilderness to look at. The whole way, he kept thinking about the meeting with Brad. He hoped it wasn't all just some con or some lame pervert looking to have their kicks. He had high hopes for the possibilities. The bus finally pulled into the station and he was off on foot to the coffee shop. When he got there, Brad was sitting there at a table waiting for him. First impressions were good. Brad was a little older than he was maybe mid to late 30s, short blonde hair, fit and he was dressed very well in a button shirt, tie and a pair of dark slacks. Overall, he seemed like a clean cut normal guy. He felt a little relived at that. He introduced himself and sat down. Brad started the conversation. "Welcome to LA! First things first. Let's get some coffee for you. I didn't know what you'd want so I decided to wait for you." After they ordered, Brad continued. "I'm glad you made the trip to come meet with me. I'm sorry about all of this but you never know who you're going to get when you place an ad on craigslist. I've conducted a few of these meetings and the guy always either turns out to be a wacko or someone I'm not looking for. Can you tell me a bit about yourself?" Nate proceeded to tell him all about himself. Of course he left out his personal details. He didn't know this guy yet so there was no need to get too buddy buddy until he knew he could be trusted. The conversation was very pleasant. It wasn't long before they were both laughing and talking like lifelong friends. Then Brad asked him a few direct questions. "Well I can see by the look of you that you aren't some weirdo or anything but I have to ask these questions just to make sure you're the right candidate. Are you drug and disease free?" Nate explained that he was as clean as a baby. He'd never even seen drugs let alone used them and as far as he knew, he was as healthy as anyone. This seemed to please Brad. He smiled and said that he had passed the first test with flying colors. Then he asked him to do something strange. "Could you stand up and do a little spin so I can see you from all angles? I know it's weird but I'd like to be 100% sure you're the right candidate for me." Nate thought for a moment. This was a weird request indeed. He stood up and did as he was told anyway. Then Brad asked him his height and weight. Again, it seemed very strange but Nate answered him with a little hesitation in his voice. Upon hearing the hesitation, Brad said, "I know they are weird questions. It's okay. I'm a doctor. Well, a plastic surgeon to be exact. It's just in my nature to ask these things. A healthy weight is essential for good health is all." This seemed to relax Nate a little and they both laughed it off. After another few minutes of conversation, Brad proclaimed that Nate seemed like the right candidate. "Well you passed with flying colors Nate. I'm very glad to say that you are what I'm looking for. You're clean, healthy, have a great sense of humor and you're someone I could feel safe sharing what I have with. When can you move in?" Nate was very excited. This long shot sure seemed to have paid off. He exclaimed that he was ready whenever he could arrange it. He explained that he didn't have much at all and just one trip back to his parents' house should be all he needed to gather all of his things. He said he'd have to look at the bus schedule to figure out when he could make it happen. Then Brad shocked him again saying, "Don't worry about the bus Nate. I'll drive you back right now if you want. No need to waste any more money on a bus. I won't have my friends taking public transport. Not when I have 6 cars I could use any time I want. What's mine is yours now." Nate was beside himself. This guy really seemed like the best guy in the world. He agreed to have Brad take him back home to gather his belongings. For some reason, he just trusted Brad completely. He seemed like the best friend he'd always wanted but could never find. They both got up to leave and Brad paid for their coffees. Nate was amazed by the awesome car Brad had. It was an Aston Martin DB9. He had seen a few photos of them but he never thought he'd actually be able to ride in one. They were very expensive cars and something that Nate could never afford in a million years. Their conversation continued all the way back to Nate's parents' house. They talked about all sorts of things. Nate began to really open up to him. He explained that his family never liked him. He said it was as if they didn't even care that he existed at all. Brad listened intently feeling sorry for the life that Nate must have been living up to this point. He explained that where he couldn't relate, he could understand. He had heard stories like that before. When they arrived at Nate's parents' house, Brad asked him if he'd like help getting his things. Nate explained that he really didn't have much at all and he could just wait for him for a few moments. Brad added that he didn't need to bring anything that couldn't be bought. Nate smiled and walked into the house. It only took him 15 minutes to gather up all of his clothing into one big suitcase. He even opened his trunk under his bed and emptied all of his feminine things into the suitcase as well. When he was finished, he walked into the living room where his mother was sitting watching TV. Of course she was drunk and didn't even look up when Nate told her goodbye. He explained that he wouldn't be coming home again and he found a new place to live. Now you'd think that a mom having heard this would ask questions but she didn't. She just didn't care at all. She just said, "Yeah yeah." Nate turned and walked out the door for the last time. Brad took the suitcase from Nate and put it in the boot of the car. They were then off back on the road to Nate's new home and he hoped, a new life. The drive back was uneventful. They continued to talk all about Nate's old life; his wants his dreams and eventually his desires. Of course he left out all of his more personal details meaning his feminine side. Nate kept that a very guarded secret that he had no intention of sharing with anyone let alone his new best friend. They pulled up to a large closed and secure gate. It was the kind of gate you see in the movies. It even had a giant B.D. insignia that Nate assumed was Brad's initials. Brad pushed a button on the roof of his car and the giant gate swung open automatically. When it was fully open, Brad drove up the long driveway until they came to the biggest garage Nate had ever seen. It could fit 10 cars easily. Brad pulled the car into the garage and closed the doors behind them. When he got out of the car, Nate couldn't help but marvel at the cars that were in the garage. They were all very nice and clearly very expensive. Brad noticed Nate's gaze and said, "Don't worry man. You'll get to drive any one of these toys whenever you want. As I said, what's mine is yours now. We'll have plenty of time to check them out later. For now, let's get to the house. I'll grab your suitcase." Brad retrieved the suitcase from the boot of the car. Nate tried to take it from him but Brad insisted of carrying it for him. He said, "Don't worry man, I have it. It's a little heavy and I don't want you to have to carry it. Just look around and take in your new life." Nate wasn't going to argue. The case was a little heavy and if Brad wanted to carry it for him, that was fine by him. Upon exiting the garage, Nate finally saw his new home. It was massive. The design was clearly very modern. There was glass everywhere. Huge windows that allowed a glimpse into the home covered the entire place. As they walked closer to the front door, they had to pass by the in- ground heated swimming pool. It was all lit up with blue lighting under the water which gave it a very cool look. Brad looked at Nate and said that the pool was a new addition. He had just had it installed last year. He added that even the deck was heated. Nate had to pinch himself once or twice just to make sure he wasn't dreaming. This place was incredible and they haven't even got inside yet. They finally reached the front door. Again, the door was marked B.D. Brad pulled out his key and hit a button on it to open the door. Even the front door was automatic. They walked inside and the inside was just as impressive as the outside. It was too beautiful for words. Brad put Nate's suitcase down and said, "Okay, time for a little tour. Follow me please." Brad led him into room after room each one being more impressive than the last. Nate counted 8 rooms so far. He realized that he could have fit his entire parents' house into just one of the rooms. 6 rooms later, the tour was over. Nate asked meekly how much a house like this cost. Brad replied, "Oh I think when it was all said and done, it cost me just about 4.5 million including the pool. I actually got a great deal. I designed the whole thing myself and had it built to my specifications. That's always the best way to go. That way you know exactly what you're getting. No sense in spending that kind of money if you're not 100% satisfied. Anyway, it's time I showed you to your new bedroom. Please follow me." Nate just nodded his head and followed close behind as Brad took him back to the foyer to retrieve his suitcase. Again Brad insisted on carrying it for him. They walked upstairs and down a long hallway until they came to the closed door of his new bedroom. Nate was in for a big shock when Brad opened it. As soon as they got inside, Nate stopped dead in his tracks. He looked around the giant room and saw that it was definitely a girl's bedroom. Everything about it screamed female. The colors, the furniture, the drapes, everything was very feminine. There was even a large vanity desk with a mirror. He remained silent for a full minute until Brad said, "I'm sorry man. This was my ex-girlfriend's room. I know it's very feminine but I haven't had a chance to get it remodeled just yet. I keep meaning to call the design crew but I just haven't yet. Don't worry though, I'm sure you can deal with it until we can have it done the way you'd want it." Nate just laughed and said that of course it would be fine. He'd make due. He added that the room was very nice even if it were a little too pink. Brad giggled and said, "Good. I was hoping you wouldn't mind too much." With that, he placed Nate's suitcase on the king sized bed and said, "Okay. I'll leave you alone now so you can unpack. When you're putting your stuff away, you'll find that my ex left a lot of her things behind. She told me she didn't need them anymore. Again, I haven't had a chance to pack them all up for the goodwill place. Whatever you find, just push it aside to make room for your stuff. There should be some room. If you need anything, I'll be in the kitchen. See you in a bit." With that, he walked out and closed the door behind him. Nate just stood there for a moment taking in everything he had just seen. He couldn't believe his luck. Not only was this place incredible, it was a dream come true! Never in a million years would he have envisioned himself living in a place like this. Brad turned out to be the best risk he'd ever taken. He was super sweet and kind. He never had a friend like that and most likely, he'd never find another one. This whole situation made him tear up a bit. Here was a kid that came from nothing that was given everything he could ever want in the matter of a day. He dried his tears and walked over to his suitcase to start unpacking. He first took out his feminine treasures and placed them on the bed next to the case. He then took out all of his male underwear and walked over to the large white 4 drawer dresser in the corner of the room. When he opened the top drawer, his heart skipped a beat. It was full of women's underthings. Silky panties of all colors shapes and designs all neatly folded lined the drawer. He quickly looked over his shoulder at the closed door before taking a handful of them out to examine them more closely. Many of them actually still had tags on them. They were brand new! Upon feeling the silkiness, his cock started to stir a bit. He glanced over at the feminine things he cherished lying on the bed only to realize that they were nothing compared to the things in the drawer. His mind started to wander. He was alone right now. Brad was downstairs all the way across the house. No one would see if he just played a little. He quickly took his pants and underwear off and picked out a very pretty pair of blue/black silk panties from the drawer. He bent down and stepped into them, loving the feel as he always did. He pulled them up and pushed his stiffening cock down and into them. He decided that he would wait to play with himself until later. He stood there in panties and pushed the rest aside so he could fit his boy things in the drawer next to them. With that done, he walked back over to his suitcase and took out a few of his undershirts. He walked back over to the dresser and opened the next drawer. He was hoping he'd find more feminine things in there and he wasn't disappointed. Inside were all of the matching bras to the panties in the top drawer. There had to be 20 or so in there! He again took some out to see them up close. Then he saw the matching blue/black bra to the panties he was wearing. His excitement got the better of him and he found himself taking off his t-shirt and slipping the bra on. To his amazement, it fit perfectly. The cups were empty but the band felt like a good fit. By now his cock was getting very hard. Here he was in a beautiful panty and bra set standing in the most feminine room imaginable. The fact that Brad could come back at any moment heightened the experience a little. It was all too much for him. He fought it though. He still had a lot of exploring to do and clothes to put away. He again pushed the bras aside and placed his undershirts into the drawer. This time, instead of going back to his suitcase, he decided to check the rest of the drawers first. He opened the third drawer and found it full of stockings and pantyhose of all colors. For a second, he thought of putting some one but that was a bit too far right now. There would be plenty of time to try those on later. He closed the drawer and opened the next one. It again was full of feminine things. Nightgowns and sleep wear to be exact. Everything was so sexy. He couldn't find anything made of boring cotton. Everything was silk or satin. Again he fought the urge to put one on. He closed the drawer and walked over to the closet. When he opened the door, he found that it was a big walk in type of closet. It had shelves and rows of hangers. He turned on the light and found it was full of dresses, shoes, skirts, and tops. There was everything a young girl could ever need in there. He walked through them all looking at each one. Many of them again had the tags still on. He giggled to himself; "If this is the stuff Bard's ex left behind, what in the world did she take with her?" Knowing Brad though, she most likely had the money to buy 100 of these closets full of this stuff. He made some room and took a few of the empty hangers so he could use them to hang up his own things. When done, he looked down at a pair of black 5" heeled pumps. He slipped his foot inside one of them expecting them to be way too small for him but to his amazement, the shoes fit. He slipped on the other one and just stood there. Here he was dressed in a matching bra and panty set wearing sexy high heeled shoes. Knowing all of his male clothes were put away, he decided it was time to play. He walked as carefully as he could back over to the bed and sat down. He looked down at the old feminine things he brought with him and smiled. He said out loud; "Well it looks like I don't need you anymore." He then reached down and let free his rock hard cock. All it took was a few strokes and he was ready to blow. He grabbed a pair of his old panties and caught all of his cum inside them. Something he never would have done if he actually cared about them anymore. When he was done, he put the soiled pair back into the suitcase along with the others he brought with him and placed it in the back of the closet. Just then he heard Brad yell upstairs that dinner was ready. He quickly got embarrassed. It jolted him back to reality. He yelled back that he'd be down in a few minutes. Like lightning, he took the shoes off along with the panties and finally the bra. After putting everything back where he found them, He got dressed in the clothing he came in walked out of the room and downstairs to the dining room where Brad was waiting for him. Brad laughed and said, "I thought you might have gotten lost up there. You were up there for quite a while. I hope the room didn't put you off too much. I know it's very feminine. I can call tomorrow and have a crew come out to paint it if you want." Nate thought for a minute. He didn't want that to happen. In his mind, the room was perfect. He loved every feminine inch of it but how could he get Brad to keep it that way and not sound fishy? Then it hit him. He said, "Naw. It's okay. I like it the way it is. In a weird way, it reminds me of my mom. I do love her. It's the closest thing I can get to having her in my life without having her in my life. If you can understand that anyway. Does it make sense?" Nate started to get red in the face. He knew it really didn't make sense but he hoped that Brad would let it slide. Brad looked at him and smiled. He said, "I understand perfectly. No need to be embarrassed. It makes perfect sense. For now, we'll keep it that way. If you change your mind though, just let me know. What about all the clothes up there? Was there enough room for your stuff? We can always just box up all that stuff and get it to the goodwill store." Nate again had to think fast. There was no way he wanted to lose all of that stuff. There was a lifetime of feminine awesomeness up there. He wanted to try on everything again and again. He decided that if the little white lie worked the first time, maybe it would work again. He said, "I have plenty of room. That's not a problem at all. I don't mind having that stuff up there at all. It reminds me of my mom too. I can deal with having the stuff up there. It's perfectly fine." This time Nate knew that it sounded weird. There was no way that made sense. His mom was in her late 40's. There was no way she was wearing anything like that. All of those clothes up there were designed for younger women. He braced for impact and the sure embarrassment that was headed his way. This time he turned visibly bright red. Brad seeing his new shade said, "It's okay man. Just calm down. I understand. Just consider all of that stuff up there to be yours. You can do whatever you want with it. If you decide to get rid of it, just let me know. There's no need to be embarrassed. We'll drop it for now okay?" Nate was taken back. What did he mean by all of the stuff was his now? Did he know his secret? He had to say something to defuse the situation. He couldn't have Brad thinking he was some type of pervert. He quickly said, "Well, thanks man, but I didn't mean I wanted the stuff! What would a guy like me want with all of that girly stuff? I just meant that it's nice to have around is all. It reminds me of when I was little and my mom used to wear that stuff. That's all." Brad laughed again and said, "Okay okay. I didn't mean anything by it. I just wanted you to know that I didn't care what you did with the stuff. Throw it out, keep it up there, do whatever you want with it. It's fine by me. Anyway, let's eat! I'm starving." That seemed to calm Nate down a little. The change of the subject was a very welcome thing indeed. He was just as hungry as Brad so they both started to eat. Brad prepared a chicken dinner. It was done very nicely. Everything was very tasty. Not only was Brad an awesome guy, he could cook like the best of them too. They both ate until they were stuffed. After dinner, Nate helped Brad clean up the dishes and then they both went into the entertainment area of the house. It was full of anything anyone needed to pass the time. There was a giant LCD TV with about 300 channels, Xbox, PlayStation, Nintendo Wii, a giant collection of Blu- Ray movies and about 50 games to play. There was even a pool table and a few real pinball games. Brad sure knew how to have fun. After a few hours of trying just about everything once, it was getting pretty late. Brad said, "Okay man. I'm pretty tired. I'm gonna hit the sack. Feel free to stay up as late as you want and continue but I have to get up early. I have a few surgeries to do tomorrow. If I don't get a good night's sleep, I'll likely give some poor girl lopsided breast implants." They both laughed at that one. Nate said he was a little tired as well so they both went walked upstairs to retire. As they got to the top of the stairs, Nate waited for a second to see where Brad's bedroom was. He was relieved that it was all the way across the house from his. That meant that he could play in his new feminine treasures without having Brad right next door and possibly over hearing something. Nate went into his room and closed the door behind him. He quickly got undressed throwing his clothing into the laundry hamper in the corner of the room. He then walked over to the dresser again and opened the drawer that contained all of the nighties. He stood there for a few minute looking through them all. He took each one out and examined it closely. He couldn't believe how many there were. There had to be 20 or so. Each one was sexier than the last. He decided on a cute Pink/Brown one that was made of silk and lace. He loved the feeling of it. He slipped it over his head and found that it fell down to just above his knees. He then opened the drawer that contained all of the panties. He picked out a pink pair and stepped into them. He pulled them up and tucked his cock back so it wouldn't show. He was so excited. This would be the first time that he could actually wear such pretty things to sleep in the whole night. He would just have to make sure that he woke up early and took them off just in case Brad popped his head in to say goodbye in the morning. He got into the bed and set the alarm clock for 7 am. He figured that should be plenty early enough. When done, he turned the light off and laid back to again thank his lucky stars for what he'd been given. It didn't take long before his eyes closed and he was fast asleep. His dreams that first night were full of feminine wonderment. There was nothing sexual about them. They consisted of him being dressed and fully made up walking through a field of flowers. He felt at peace. It was a sure sign of a well content mind. The alarm clock went off at 7 am. Nate reached over and turned it off. He found that in the night, he must have gotten a little too warm because the covers were pushed way down. He looked at the door to the room and listened for any sign of movement. He heard nothing but silence. He got up and quickly took off the nightie. He left the panties on though. He got a pair of his jeans and t-shirt and put them on. He then opened the door to his bedroom and walked into the hallway. When he got to the top of the stair case, he listened again. Still he heard nothing. He walked over to where Brad's bedroom was and found the door wide open. When he peaked inside, he saw that Brad had already gone. He thought to himself, "Wow. When he said he needed to get up early, I guess he meant really early. A slight bit of panic set in. He hoped that Brad didn't try to say goodbye this morning because if he opened the door, he surely would have seen Nate dressed in the pretty nightie. He decided there was no sense in worrying too much about it just yet. He then walked downstairs to the kitchen and saw that Brad had left him a note that was attached to the refrigerator. The note said, "Good morning! I hope you slept well. I have a bunch of surgeries scheduled for today so I'm afraid you'll be alone until about 4 o'clock or so. Feel free to do whatever you want. Explore and have fun. Just be yourself. PS. I left something for you in the microwave. I hope you like French toast......... Brad." The part about the French toast was welcome but what Nate didn't understand was the "explore" and "Just be yourself" bit. What did he mean by that? Paranoia started to set in again. Did he know Nate's secret? It made Nate a little uncomfortable. After last night's conversation and the fact that he got red faced when Brad said something similar, he couldn't help but feel a little worried. He tried not to let it bother him too much though. He thought, "I'm sure he doesn't mean... well that. He probably means to explore the house. That's all." He calmed himself down and got the French toast from the microwave. It was still pretty warm so he must have just missed him. He ate it all and cleaned up. When he was finished, he went to the entertainment room and started to look through the movies. Then he realized something. By this time, it was about 8 am. That meant he'd have 8 full hours of being alone in the house. The draw of his alter ego Jade was too strong for him to resist. He had a whole room of feminine awesomeness to play with. He had the whole house and plenty of time. He found himself walking back upstairs to his bedroom and looking through the walk in closet. He went through row after row of pretty dresses all of which were very pretty. He picked one out and held it up to himself. It was a very pretty white and tan floral print sun dress. He took it and brought it into the bedroom. He placed it carefully on the bed and started to get undressed. When he was naked, he looked down at his legs then at the dress. The dress at most came to his knees. That meant that his hairy legs would be visible. Up until now, he was a little scared of shaving them because of school but knowing that school was over, there really was no reason now not to have silky smooth legs. He heisted for a moment. What if Brad saw his shaved legs? Then he realized that Brad hadn't seen his legs before. Maybe he could get away with it by telling him he never really had much hair to begin with. That's if it ever came up anyway. The possibility of having smooth legs while wearing the dress was too much for him. His cock was already getting stiff just thinking about it. He had to do it and deal with whatever consequences came after. He walked naked out of his bedroom and down the hall to the bathroom. When there, he started looking around for something he could use to get the job done. Then he saw a cabinet near the shower and opened it up. He was thrilled to see that Brad's ex must have left some of her stuff there too. There were a bunch of packages of ladies' razors and a few cans of feminine shaving cream. He gathered what he needed and got into the shower. His face wasn't a problem. It was still smooth as ever. He never really started to develop facial hair which made his dress up time all the easier. Having never shaved his legs before, he really didn't know where to begin. It took quite a while but he finally got the job done. For a first timer, he did a pretty good job too. There were only a few small nicks. When his legs were done, he decided that since the dress was sleeveless, he might as well shave his underarms as well. He had a bare chest and stomach already so there was no need to go there. He then washed and conditioned his long hair. When he was finally done, he got out and dried himself off. He couldn't get over how different his legs felt. It's not like he was super hairy to begin with but having them shaved smooth sent shivers up his spine. He loved the feeling and decided that he'd keep them that way from then on if he could get away with it. He then walked back into his bedroom and went right to the dresser to pick out his underwear for the day. There were so many styles and colors to choose from. Finally, he decided on a pair of pink and red panties with lace trim. He found the matching bra and put them both on. By now, his cock was getting very hard. He decided that he had plenty of time to play with that later. He was just beginning to get dressed. He fought with it until it got soft enough to push pack into the panties between his legs. It was finally time for the dress. He picked it up and saw that there was a zipper in the back. He unzipped it and stepped inside. He relished in the feeling of pulling it up over his smooth legs. When it was fully up, he slid it around to zip it up. After a few moments of fidgeting with it, he got it done. He slid it back around and put his arms into the straps. When he was done, he walked over to the full length mirror to see himself in a real dress for the first time. He loved what he saw. His heart was pounding. There was a bump in his throat. He was even shaking a bit. He stood there for a full 5 minutes until he remembered the vanity desk in the corner of the room. He hoped that he would find at least a few cosmetics in the drawers. After all, Brad's ex left so much stuff behind; surely she left some makeup too. He sat down and started to open the drawers. He wasn't disappointed either. Inside were various shades of eye shadow, eyeliner and what looked to be 10 or more tubes of lipstick most of which weren't even opened and still had the safety seals intact. He felt relieved that he wouldn't have to resort to using the few things he brought with him. They were old and not very appealing anymore to him especially now that he had all of this stuff to play with. He spent the next hour playing with different techniques of makeup application until he was satisfied. He was so grateful to all of those girly magazines he had collected over the years. They all of them had a few articles of makeup application. He learned them all by heart. It wasn't until now though that he could really put his skills to use being there was so much he had to work with. His eyes were now shadowed with a very sexy brown pink combination and his lips were frosted with a reddish pink lipstick. With that done, he decided it was time to do something with his hair. His face and clothing were far to pretty to just do nothing with it. He wanted the full effect so to speak. He found a hair brush in one of the drawers and started to brush out the tangles from his hair. It had already air dried quite a bit so he worked with it until he was satisfied. He pulled it back and up high on the back of his head and used a scrunci to hold it there. He then pulled a few loose strands down in front to frame his face a little. When he was done, he looked through the drawers again and found a few bottles of perfume. He picked one out called "Chanel. Chance" and sprayed in on his neck and a little on his chest. He loved the flowery smell. It was a little strong as he put on a bit too much but he didn't care. With everything done, he got up and walked over to the full length mirror again. He was in love with the girl looking back at him. He was very pleased at what he accomplished. He went from normal boy to a very pretty girl in a matter of a few hours. It was a dream come true for him. He looked at the clock on his bedside table and saw that it was about 12. That meant that he'd have another 4 hours or so before Brad got home. He walked back over to the closet and picked out a pair of tan strappy sandals with a 3" heel on them. After putting them on, he declared that he was finished and Jade was ready for her day. He walked as best he could to the bedroom door. He poked his head out to make sure Brad hadn't come home early. Hearing nothing but silence, he took his first step into the hallway. He loved hearing the click of his heels on the marble floor. Now I don't want you to think he was walking all that gracefully. He was still very unsteady on heels but he managed slow and small steps to keep his balance. He gingerly walked downstairs to the entertainment room again and returned to looking through the movies. He decided on a girly sounding movie he had never seen before. Maybe it was the way he was dressed or maybe it was the way he was feeling. It didn't matter. He was Jade and Jade wanted to watch it. After popping it into the player, he sat down and relaxed on the couch. It turned out to be a pretty long movie. It wasn't over until about 3 o'clock. He figured he had about an hour or so left before he had to go and change himself back to normal. He sat there on the couch thinking about what he wanted to do next when he heard someone walking up to the front door. Panic set in. He jolted up and ran over to the window to see Brad approaching the door. He turned and started to run for the stairs almost falling over because of the heels he was wearing. He managed to get all the way upstairs as Brad opened the door and walked in. He hurried around the corner and down the hall towards his room. When he first came out of his bedroom hours ago, he loved the sound of his heels clicking on the floor but this time he hated it. He tried to walk as softly as he could so Brad didn't hear. He finally got to his room and hurried inside practically slamming the door behind him. He then began to get undressed as quickly as he could. The whole time his was taking off the clothes, he couldn't help but be paranoid. He wasn't fully out of sight when Brad came in the door. There was a chance, all be it a small one, that he saw him hurrying around the corner. That would be very bad. Brad was so nice to him giving him this awesome free place to live. The last thing he needed was for Brad to find out his secret. What would he think of him? He was sure that Brad would throw him out for being a pervert. When he was just about naked, Brad yelled upstairs and said, "Hey Nate. Is everything okay?" Nate was scared. He didn't know what to reply. He couldn't sound panicked. That would be a dead giveaway and make Brad ask more questions. He squeaked out a, "Ummm Yeah! Everything is great! I'm just.... getting changed. I'll be out in a bit." He hoped that would do. He didn't hear a reply though. He ran to where he put his boy clothes before and started to get dressed. After a few minutes, he heard Brad knock on his bedroom door. He began to panic again. Sure he was dressed back in his boy clothes but he was still fully made up and everything he wore including the dress and lingerie was thrown all over the bed. He yelled, "Hey I'm getting dressed. I'll be out in a minute okay?" Brad replied, "Okay man. I just wanted to make sure you were okay. From the sound of your voice, you sounded like something was wrong. Take your time. I'll be downstairs." Nate walked carefully over to the door and he heard Brad walking away and down the stairs. He started to feel more relaxed. He may have dodged the bullet after all. When he was sure the coast was clear, he hurried out of his room and quickly walked over to the stairs. He could hear Brad far away. He ran past the staircase and into the bathroom. He then began to scrub all of the makeup off of his face. As he was cleaning up he cursed himself for doing everything he just did. How could he be so stupid? He should have changed back to normal hours before this. He didn't want his little hobby to ruin everything he was given after only one day. He vowed to be much more careful after this. The guilt and shame of the whole thing made him start to hate himself and what he was. When he was fully back in boy mode, he went back to his room and put away all of the clothing he left on the bed. With everything cleaned up, he went downstairs to find Brad sitting in the living room reading a book. Wanting to diffuse the whole situation he asked Brad how his day was. Brad looked up from his book and said, "Oh it was pretty good. I can't complain. All of the surgeries went very well. How about you? How was your first day here? I hope you found ways of passing the time." Nate sat down near Brad. He replied that his day was great and all he did was watch a movie. He hoped that would be the end of the whole thing but Brad said, "Hey I'm sorry I came home a little early. I thought one of the surgeries would take longer than it did. I hope I didn't scare you. The last thing I want to do is make you feel uncomfortable here. Maybe I should have called first." Nate had no idea how to reply. From the way Brad was talking, it seemed that he knew something was up. Why else would he feel bad about coming home early? This was his house after all. Seeing the confused look on Nate's face, Brad said, "Look. It's okay. You don't need to be embarrassed. Really... You don't. I understand fully. I knew who and what you were before I agreed to have you live here with me. You don't have to hide yourself with me." Nate looked at him and his eyes got as big as saucers. He knows? Oh no! He started to stammer and stutter asking what Brad meant. Brad said, Just calm down. It's okay. You don't have to say anything. Just hear me out okay? I knew you were different when I first saw you. In fact, it's what made my decision to bring you here. I've been looking for someone like you for a long time now. I told you I conducted many different interviews with other potential candidates to live here with me. One of the things I was looking for was... well... a young boy that had a strong feminine side. Someone that I could help make their dreams come true for them. You may be wondering how I knew just by looking at you and talking with you. Well, I know what to look for. It's become almost an art. There are a few subtle things that are dead giveaways. The way you talk, walk, and conduct yourself for example. It's all slightly feminine. That mixed with your feminine appearance and long hair told me you were the one I was looking for. After seeing your reaction to your bedroom and all of the pretty things up there, I knew I was right. Now there's no need to be scared or embarrassed about it. Like I said before, this is a place that you can just be yourself without fear of being found out. Do you understand?" Nate stayed silent. He had mixed emotions. On one hand, his secret was out and someone knew. That would usually be a very bad thing but listening to the way Brad was softly talking to him about it made it all seem okay. He wasn't judging hm. He wasn't telling him it was wrong. He was accepting and in fact, even encouraging him. It was something that Nate never thought he'd have. A friend that not only was okay with his cross-dressing but he was very cool with it as well. Brad continued, "Now I know this is a lot to take in so we can drop it right now if you want. I don't want you to feel uncomfortable with the whole thing. Just know that you don't have to hide anymore. When you're ready to talk about it, I'll be here." With that, Brad looked back to his book and continued to read. Nate just sat there thinking about what to say. Then he asked about all of the clothes that were left in his bedroom. Were they really his ex- girlfriends or were they put there on purpose? Brad looked up again and said, "No. That's true. Most of that stuff is my ex's. She lived here with me for a few years. I did add more though after she left in hopes that I'd find someone that would appreciate it as much as she did. Before you ask, yes..... she was a girl not unlike you. I found her in the same way I found you. When she started living here with me, she was a boy. I helped her become the woman she was inside." Nate saw that Brad started to get a little sad. He asked what happened with her. Brad sighed and said, "Well, to be honest, I don't really know. Everything was going great. I really thought she was happy here. Then one day she said she was leaving me. She made an excuse that she wanted to go and live someplace else now that she had everything she ever wanted. I thought she loved me but it turned out, she used me to get what she wanted and then left me. I tried talking her out of it but she got really cold. There wasn't anything I could say or do to keep her so I wrote her a check for 5 million dollars and told her I wanted her to be happy and safe even if it wasn't with me. That was about 2 years ago now." Nate saw the look of pain on Brad's face. He really did seem to care very much for the girl. He couldn't be sure but he thought he could see tears in his eyes when he said the last part. Nate decided to change the subject. He said, "Okay, so now what?" Brad smiled and said, "Now you get to be you. I don't want you to think I'm doing this just to have another girlfriend. I in no way want you to think I brought you here to be my lover. I don't know what your sexual orientation is and to be honest, it doesn't matter. I just wanted to give someone like you a chance at being yourself. It's up to you to decide how far you want that to go. While you're here, the possibilities are endless. You can walk away right now if you want. I'll make sure you get back to your old life with no questions asked. Everything from now on is up to you. We both know the whole truth now. So, what will it be? Do you want to stay here, or should I get the car ready to take you back to your parents' house?" Nate didn't hesitate at all. He just said, "So when's dinner? I'm supper hungry!" Brad smiled again and said, "How about takeout? I know of a great Chinese place that has the best General Tso's chicken in California!" Nate laughed and said that sounded great. The heaviness of the room lifted and things got back to normal. Well, normal in the sense that it could be anyway. Brad got up and called the restaurant to order. When he was done, he looked at Nate and said, "Now there's no pressure at all but..... Who am I going to be eating with tonight? If you're not ready, I totally understand but I'd like to meet the real you. It's been a while since I ate with a lady." Nate thought about it. It would be the first time anyone had ever seen him while full dressed and made up. He was a little nervous but he decided it was going to happen sooner or later. Why not get it over with now? He said he needed to get "dressed" for dinner. Brad smiled again and said, "Okay, I'll be waiting. Take your time. Chinese food has a way of staying hot for hours!" They both laughed at that as Nate went back upstairs to his bedroom to get ready. He was both excited and nervous. He wanted to look his best. The last thing he needed was for Brad to think he looked silly. He knew that he had what it took to look good but he'd never had to pass in front of another person before. He hoped he was as good at making himself beautiful as he thought he was. Having showered and shaved his whole body earlier that day, he knew that he could go right to getting dressed. Now was the big question. What was he going to wear!? He walked over to the walk in closet and went inside. There was almost too much to choose from. He took out dress after dress and held them up to himself. They were all great but he really didn't know which one to choose. Then he though back to the movie he watched earlier. The girl in the movie wore a little black dress when she went out to dinner so he figured that was a good place to start. He looked though them all until he found the perfect one. It was a sleeveless black dress with spaghetti straps and lace that accented the neckline. He held it up to himself and found that it was a little short. It barely came to mid-thigh. For a moment, he thought that it might give the wrong impression. The last thing he wanted was for Brad to think he was trying to look slutty. It was too pretty to pass up though so he decided it would have to do. Besides, the girl's dress in the movie was even shorter than this one. He took it out and placed it on the bed. With the dress picked out the next thing he needed was the lingerie. Just thinking about wearing silky panties in front of someone else that actually knew he was wearing them made his cock spring to life. It was getting harder by the second. He walked over to the dresser and opened the drawer that contained the panties. It really didn't matter which ones he wore because he had no real intention of Brad seeing them. The thought did cross his mind though even if it were only for a second. He still wanted to pick out the perfect ones. Looking through them, he came across a sexy red pair with little black bows. He turned and tossed them over to the bed. He then opened the next drawer and found the matching bra which he also threw over to the bed. For a moment, he wondered if he should wear stockings. He decided against it though. He wasn't even sure how to put them on and he didn't want to ruin them. He'd have plenty of time to experiment with them later. He walked back over to the bed and started to get undressed. When naked, he stepped into the panties and pulled them up over his hard cock. He then put the bra on. Something didn't seem right though. He wanted to fill the cups with something. When he was alone, it was never really an issue but this time someone was going to actually see him. He wanted the full effect. He walked back over to the dresser and took out a few pairs of the panties and stuffed his bra with them. Instantly, he felt better. He walked back over to the bed and stepped into the dress. It was made of stretchy material so there was no zipper this time. He pulled it up and put his arms through the straps. It was amazing to feel and see the difference with having the cups of his bra filled. It actually gave him a much more feminine figure. He decided right then that he would stuff the cups from then on. Being fully dressed, the next step was to do his face again. He walked over to the vanity table and sat down to get started. Since it was the evening, he knew from the girly magazines that he should do his makeup a little darker than before. Most cross-dressers don't realize it but there are different styles for different times of the day; lighter and softer tones during the day and darker more bold shades at night. He wasn't exactly sure why but he knew it was the way most women did it from reading the magazines. He picked out dark grey shadow for the outer corners of his eye lids and a lighter blue for the inner and middle. Blending it all is something that is essential. If you don't blend it just right, it looks silly. It took him many nights of experimenting until he got it down pat. With that part done, he lined his bottom lids in black and added a little mascara to bring out his already long eyelashes. Blush really wasn't needed. He already had a reddish pink hue to his cheekbones. Adding more would make him look clownish. Lastly, he needed to pick the right shade of lipstick. He decided on a reddish brown. He took the cap off and swiveled the color stick up. He applied a good amount to his bottom lip and then a lighter amount to the top. He knew better then to add it to the corners of his mouth. That never looks good no matter what shade it is. When he was done, he brought his lips together, mover them back and forth a little and blended it all together. He looked into the mirror and loved the job he had done. It's amazing what makeup could do to your face when done right. He still needed to do something with his hair. He decided to do the same style as earlier today. It was cute and should accent the look he was going for nicely. Lastly, he sprayed on a little of that perfume he wore earlier that day. With everything done, the only thing he needed was the right shoes. He got up and walked back over to the walk in closet. At first, he was going to wear the sexy pair of black pumps that he put on when he was first alone in the room yesterday but then he realized they had a 5" heel on them. There would be no way he'd be able to walk in them. Not gracefully anyway. He didn't want to look like a stumbling idiot in front of Brad. He looked though the shoes until he found a similar pair but the heel was only about 3". He put them on and practiced walking back and forth a few times to get used to them. When he was satisfied that he could get around without wobbling too much, he walked over to his bedroom door and peaked out. Brad was still downstairs waiting for him. He could smell the distinct smell that only Chinese food gives off so he knew the food had gotten there. Now came the moment of truth. He hesitated for a few seconds before walking out of his room and down the hall to the top of the staircase. His heart was pounding faster and harder than ever before. There were butterflies as big as dump trucks that were fluttering around his stomach and chest. His mouth went dry and felt like cotton. His cock that was rock hard just a few minutes ago went as soft and the panties he was wearing. He could just call the whole thing off and yell to Brad and tell him he wasn't ready to do this yet but he didn't. He took a step down the stairs followed by another and another. Eventually he was at the landing. He stopped there for a moment to catch his breath and calm himself down a little. It wasn't working though. He looked around and heard that Brad was in the dining room. He slowly walked over until he was just around the corner to the room. This was it. One more step and he would be in plain sight. Part of him wanted to turn around and run back upstairs but an even bigger part just wanted to get it over with. He took a deep breath, let it out, and stepped around the corner. Brad was sitting at the large dining table looking down as he was just getting done setting the table for dinner. When he heard the telltale clicks of high heels, he looked up and saw Nate. He just looked for what seemed like a million years. Both of them remained very quiet. Nate started to feel uneasy. Did he think he looked terrible? Did he think he looked like a train wreck in a dress? Finally, Brad spoke up and said, "Ummmm. I'm sorry... I had... No idea how beautiful you really were. You're incredible!" Nate felt relieved. From the sound of his voice, he wasn't kidding. He was serious. It made Nate blush quite a bit. All he could muster was, "Thanks." Brad got up and started to walk around the table. It startled Nate a little but when he stopped at the chair closest to Nate and pulled it out for him, he knew what he was doing. Nate walked slowly over and sat down in the chair and Brad pushed it in. He was such a gentleman. Brad walked back in front of Nate and said, "You even smell fantastic. I can't get over it. You're too beautiful for words. Really you are. I'm not just saying it. I'm being totally honest with you." Brad walked back over to the other side of the table and sat down. Nate loved hearing the compliments. It meant that everything he'd learnt over the years did actually pay off. He sat there in the chair with the biggest smile on his face that he ever managed. He looked in brad's eyes and said, "Thanks again. It means a lot to me. Doing this alone for so long, I had no real way of knowing if I was doing it right or if I was just kidding myself." Brad responded, "You are defiantly doing it right Nate. Wait. I can't call you Nate with you looking as beautiful as you are. It just seems silly. Do you have a name picked out for yourself?" Nate smiled and said, "Yes I do. I call myself Jade. I chose that name because it was the name of the first real transsexual woman I had ever seen. Her pictures were on a website that I found back when I was just a kid. She was very pretty. I guess I wanted to be just like her when I grew up." Brad smiled and said, "Jade! I love it! It's a very pretty name for a very pretty girl. From now on, if it's okay with you, I'll call you Jade. It's going to be very difficult for me to go back to calling you Nate after tonight." Nate smiled and said, "No that's fine. I always hated the name Nate anyway. Just call me Jade from now on. I'd like that very much." Brad continued, "Okay deal. Thank you very much for showing your real self to me. I consider it an honor. Really I do. I know it took a lot for you to dress in front of someone let alone someone you just met a couple days ago. I've heard that it's one of the most difficult hurdles a girl like you has to get over. It shows that you have courage and willpower. Many girls like you grow old and pass without ever sharing their true selves. That is extremely sad. I'm very glad you took this step Jade. The first step of many I hope. Anyway, I could sit here all night and continue to compliment you but the food is getting cold. They'll be plenty of time for that later. Let's eat." They both started to eat their dinner. Brad was right. It was very good chicken. Every piece was just as tasty as the last. About mid-way through Brad spoke up again, "So, why don't you tell me a little about what you see in your future? I mean I hardly know anything about what you want with this whole thing. Do you like being a boy that dresses on occasion for fun or do you want something more permanent?" Jade thought about it and said, "Well I don't really know. Up until now, it's just been a hobby but now I don't know. I love being Jade. It's like this is who I really am. Nate is just the shell I wear because I couldn't be Jade all the time. My mother never really cared about me much but I couldn't come out and tell her. She'd never understand. She's kinda religious. I know she'd see the whole thing as a sin. I'm sure she'd haul me away to some church and have them perform an exorcism on me." They both had a good laugh at that one. Jade continued, "I personally don't believe in all the god crap. It's way too farfetched. It has been something that's stopped me though because of my mom I mean. Now that I live here though, that just isn't an issue. I think I'd like to try and live as Jade; for a while anyway. I owe it to myself to give this a longer run than just a few hours locked up in a bedroom all alone. Is that okay with you?" Brad stopped eating and got a very serious look on his face. He said, "Nothing would make me happier than to have Jade around here at all times. You're right. The only way to really tell is for you to immerse yourself in it for a while. Then you'll know for sure if it's something you really want or if you just want to keep it as a part time hobby. Until you tell me otherwise, I'm going to look at you and treat you like the young beautiful girl you are at all times. You're not a he anymore. You're a she." Jade liked that idea. Finally she could think of herself and be recognized as a she or her rather than the boring he or him. It might take some getting used to at first, but it would be fun to try it out for a while anyway. Dinner was over. It was time to clean up. Brad insisted on doing it all. He told Jade to go sit in the entertainment room until he was done. She tried to object because she wanted to help out but Brad was insistent. She got up from the table and walked away making sure she wiggled her butt a little while she walked away. She couldn't be sure but she imagined Brad was watching her walk away. It gave her a tiny thrill. When Brad was finished cleaning up, he joined Jade in the entertainment room. She was sitting on the couch waiting patiently. Brad walked in and took a seat next to her on the couch. He said, "Okay Jade. Well, we have all night. What would you like to do to pass the time?" Jade thought about it for a minute and said, "Let's play a game. I saw that you have Black Ops 2. Let's shoot some people!" Brad laughed and said, "That sounds perfect!" He turned on the Xbox and they began to play. The hours flew by with both of them having a blast. Every once in a while, Jade would look over at Brad and found that he was staring at her. Not in a weird way. It was more like the way someone looks at the most beautiful painting they had ever seen. It made Jade feel even better about the way she looked. After a couple more hours, it was starting to get late so Brad said, "Okay. Well, it's about that time. I need to get up early again tomorrow." Jade was feeling tired as well. After all, she woke up pretty early herself this morning. They both agreed to call it a night. Brad turned off everything and they walked to the staircase together. As Jade started up the stairs, she began to wobble a bit on her heels. Brad was quick to grab her around the waste to steady her. It was the first time he ever got that close to her. It was a nice feeling. He then took her by the hand and they walked up the stairs together. When they got to the top, Jade turned to Brad and reached out pulling him close for a good night hug. In a tight embrace she said, "Thank you so much for being an awesome guy. You're the best thing that's ever happened to me. Really you are." It was Brad's turn to blush. He whispered back, "The pleasure is all mine Jade. I love seeing someone as happy as you are right now and if I could be part of it, that's all the thanks I need. You have a good night's sleep now. I'll see you tomorrow." With that, they split up and walked to their respective bedrooms. When Jade got to her room, she walked inside and closed the door behind her. She just stood there for a long time. All of the night's activities, what Brad said, what she said, everything was flooding her mind. It was just as perfect as she could have dreamt it could be. The possibilities were now endless. She was free to live as herself for as long as she wanted and nothing could stop her. She felt more alive in that moment than ever